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United States Patent | 5,550,288 |
McManus | August 27, 1996 |
A novel process for the preparation of .alpha.-aminoacylanilides comprises the treatment of the corresponding .alpha.-haloacylanilides with a solution of ammonium carbamate in aqueous ammonia. The process is especially useful in the preparation of certain active cardiac antiarrhythmic agents, such as tocainide.
Inventors: | McManus; James W. (Leesburg, GA) |
Assignee: | Merck & Co., Inc. (Rahway, NJ) |
Appl. No.: | 335806 |
Filed: | November 14, 1994 |
PCT Filed: | June 11, 1993 |
PCT NO: | PCT/US93/05613 |
371 Date: | November 14, 1994 |
102(e) Date: | November 14, 1994 |
PCT PUB.NO.: | WO93/25518 |
PCT PUB. Date: | December 23, 1993 |
Current U.S. Class: | 564/194 |
Intern'l Class: | C07C 235/68; C07C 237/06 |
Field of Search: | 564/194 560/14 |
2851494 | Sep., 1958 | Ehrhart et al. | 564/194. |
3210412 | Oct., 1965 | Chapman | 562/442. |
4169106 | Sep., 1979 | Diamond et al. | 564/157. |
4218477 | Aug., 1980 | Boyes et al. | 424/324. |
Foreign Patent Documents | |||
63-39844 | Feb., 1988 | JP. | |
1374367 | Nov., 1974 | GB. | |
1420067 | Jan., 1976 | GB. | |
1461602 | Jan., 1977 | GB. | |
WO91/12265 | Aug., 1991 | WO. |
"New Antiarrhythmic Agents. 1. Primary alpha-Amino Anilides", Eugene W. Byrnes, et al., Journal of Medicinal Chemistry, 1979, vol. 22, No. 10, pp. 1171-1176. "New Antiarrhythmic Agents. 2. Amide Alkyl alpha-Amino Xylidides", Paul D. McMaster, et al., Journal of Medicinal Chemistry, 1979, vol. 22, No. 10, pp. 1177-1182. The Merck Index, 10th Edition, Compound No. 518, p. 76 (1988). |